Sahil Lavingia: I started as a designer when my
middle school gave all of the students a Photoshop license for free. I started messing
around with it because I realized I had access to thousands of
dollars of software and I might as well give it a shot.

I googled Photoshop tutorials and made really weird things for
fun and kind of got hooked. I started designing websites because
that's where the money was.

When I was 14 and I was like, "I'm tired of this, I want to build
my own products."

I had all these random ideas for little things I wanted to build
so I would design them every weekend. I would get home from
school on Friday, pick one of my gazillion ideas to design and
contract out all of the back-end work. I'd launch the app by
emailing every tech blog I knew. Inevitably one of the five would
write about it and then I would sell it on some marketplace.

What ideas did you create and sell?

I built a to-do list app. I built this thing that let you create
Facebook walls but for Twitter before Twitter had any kind of
conversation aspect. I built this tool that let users send
automatic, customized direct messages on Twitter.

How many apps did you build and sell?

I built about 20. I think I sold all of them.

Whom did you sell them to and for how much?

There was this marketplace -- it's called Flippa now. I couldn't
sell them for much — maybe $1,000+.

How much did you pay to contract them out? Because you
were just the idea guy, you didn't code them yourself.

Yah that was frustrating because I do not like paying people
money. You know, maybe that's why my investors like me. But
I probably payed $50 per app.

Yeah, I mean for two hours of work for a guy who is also in high
school but lives somewhere else in the world. I found them by
Googling developer forums. I never went to an e-Lance or anything
like that. I just went to forums and tried to get someone
reputable to them. I built relationships and would go to the same
people every time.

I was also frustrated that I was paying people to build what I
couldn't. So I started learning HTML, CSS, PHP, then the
iPhone came out and I learned iOS development. One of the iPhone apps I made
was on the home page of Apple.

It's not easy to learn to code. How did you teach
yourself?

PHP was a failure. It took me two months of trying to build my
own little app and I just hated it. I gave up and figured
back-end development was not for me.

But then the iPhone came out and I learned that stuff really
fast. I learned iPhone development in 2 weeks. I downloaded
Stanford videos and those became my whole life. So
I learned iOS development when I was 16.

I was financially independent when I was 15. I never really tell
anyone that because it doesn't feel relevant, but looking back I
think, Oh, starting a company might have actually made
sense. I have been doing okay for a while. My bank account
when I was 15 or 16 was over $100,000.

Boonsri Dickinson, Business
Insider

Are your parents entrepreneurs?

My dad is in finance but he's not really entrepreneurial. They
were definitely a little antsy when I left USC.

They knew I was doing what I thought was right and were being
open minded but they had never started a company. They are both
from India.

My mom actually grew up pretty poor and my dad did okay and then
they moved to the U.S. I was actually born in New York. My mom
says the best birthday present she has ever given me is my U.S.
citizenship.

When I was four I moved to Hong Kong. One year later I moved to
Singapore. A few years later I moved to London. After two years I
moved back to Singapore and then when I was 17 I moved back to
the U.S.

I moved to L.A. to go to school at USC and I was there for four
months for the first semester before Pinterest grabbed me and
then I moved up to Palo Alto last year.

How did Pinterest find you?

When I moved to the U.S. I wanted to build a brand for myself, so
I started blogging, tweeting, and using Hacker News. That
got me attention from startups in the Valley, including
Pinterest. Pinterest sent me an email in August 2010. At the time
it was very small. I think it had less than 5,000 users.

I met up with the two founders to chat for a couple hours about
what they were doing, what they wanted to accomplish and to hear
their story. I left thinking, "Holy shit, I definitely want to
get up here."

My goal was to get a four year degree and then join an early
phase startup and maybe found one of my own. That was a 7 year
plan. Then I thought, "Wait a minute, I have the ability to skip
three years of this process; I might as well do it."

I wasn't that dead-set on Pinterest and I had a few other offers.
There were some Y Combinator companies I was considering and
Flipboard. I picked Pinterest
because it was the earliest company. My goal was to figure out if
I could found a startup or not and I felt joining the earliest
company was the best way to learn.

I stayed at Pinterest for one year and left in August, 2011.

You were there when Pinterest's traffic was exploding.
What was that like?

It was amazing. I joined Pinterest when we only had 5,000 users
but we were growing something like 80 percent month-over-month
(don't quote me on that, I'm not sure the exact metric). We had
engaged users, and which would you rather have, 10,000 users who
really love your site or 10 million users who never use it?

Before we raised $10 million from investors we were doing very
significant amounts of traffic. If you looked at the numbers, it
was clear if we just kept doing what we were doing we were going
to be successful. The numbers got bigger and bigger. Going from 1
to 2 users doesn't sound as cool as going from 1 million to 2
million.

What was your role at Pinterest?

I was the first designer and second engineer. I designed the
iPhone app and did all the front-end stuff. The two founders Paul
and Ben are both non-technical. Josh, the first engineer, did all
of the coding so when I joined I did all of the front-end stuff.
I worked on the API, all of the social sharing buttons on the
site, the about pages, and all of the mobile stuff. As a typical
early employee, I had to do everything.

What is your new company, Gumroad? Your tagline is "share
and sell anything to your followers." It turns anything you
upload and want to sell into a short url that can be shared to
personal networks, right?

Over the past 10 years sharing has become easier. Before, in
order to share your thoughts, you needed to write a book and
contribute to a newspaper or magazine. Then you had to contribute
to a blog or start one. Now all you need is a Twitter account, a
Tumblr or a Pinterest page.

Sharing information has gotten easier, but the way people sell
hasn't changed much. iTunes still takes the same fee it took 10
years ago even though the world is completely different.

I thought, if Twitter, Facebook, Pinterest and Tumblr have [given
people their own followers], why hasn't there been a
restructuring in the way people sell?

Kanye West, for example, used to have a blog and now he has just
three buttons on his entire site — a Twitter button, a Facebook
button and an iTunes button.

The way Kanye West markets is very different than the way he did
10 years ago. People have chosen to be his fans and followers; if
he wants to talk to them he tweets. But if that's the case why
does he still give 30 percent to iTunes? Why doesn't he or his
label have the ability to sell directly to his followers?

I don't think that applies just to music and Kanye West. It
applies to any person who creates content, because Twitter has
given them the ability to own their following and given them a
distribution channel. Gumroad gives them the opportunity to sell
directly.

I don't think it was possible to build something like Gumroad
5-10 years ago because you needed Facebook and Twitter to build
personal networks before the commerce piece could exist.

Here's how Gumroad turns
an item for sale into a short url that receives
payments.Gumroad

So you're saying people needed big distribution networks like
Walmart, iTunes or Amazon to reach an audience before, but now
they have their own online audiences they can sell to instead?

Yes. When iTunes first came out that was the only way you could
sell music online so they deserved to take 30 percent. Not so
anymore.

You're hoping that, along with having a Twitter feed and
a Facebook profile, people will have Gumroad links to sell
directly to those networks?

Exactly.

[See demo of how Gumroad
turns an item for sale into a short url that receives payments on
the left]

Can you only sell one thing at a time with Gumroad? If I
am Kanye West, can I only sell my one current hit with a Gumroad
link or can there be multiple Gumroad links for multiple
products?

You can create as many links as you want and we will have profile
pages to aggregate all of the things you are selling via Gumroad.

Users can link to that personal page directly and it is kind of
like a personal collection of items for sale. The personal
collections can apply to all sorts of content -- like books. Why
should you have to wait three years to release a book and see how
well it does? You should be able to release a chapter and see
results faster.

There is also an option where, if you want to sell ten albums or
ten tracks or ten photos, you can turn them into one file and
sell them as a package. So if you want to sell a ton of stuff at
once you can still use Gumroad, you just have to zip them up
beforehand.

When did you come up with the idea for Gumroad?

Even when i was at Pinterest I wasn't 100 percent sure what I
wanted to do. I was pretty sure I wanted to start my own company
but I didn't know exactly what I wanted to work on. I
talked to a bunch of people and Gumroad was really the only idea
I felt I could work on ten years from now. It was the only one
with an initial problem small enough you could grasp it and build
something people would use immediately.

I designed an image that led directly to Gumroad, the pencil icon
[see above left icon in the demo], in April or May of 2011 while
I was at Pinterest. But it wasn't like I had been thinking about
Gumroad specifically for a long time. If you go back, I guess I
had been in some way or another.

I realized I wished it was easier to sell stuff online when I was
making iPhone apps.

The thing about charging someone for a product is whenever
someone buys it, it's validation — that person thinks it is
valuable. Whereas if one million people download a free app you
have no idea if it's valuable for anyone.

How big (or small) is Gumroad right now?

We're pretty small. Two weeks ago it was just me working on
Gumroad. One of the reasons I wanted to be able to do everything
was so I could lower costs and see if I could make the thing work
before making anyone commit to an unstable vision or an unstable
product.

I launched Gumroad basically by myself in mid-Feb and my goal was
traction. If I could get traction then I would hire people. If
not, I'd keep working on it to make it better until I got the
traction. Luckily I got some traction the first time around. A
lot of my investors said I was crazy to try and get traction
before hiring anyone, but I don't really do things very typically
anyway.

Right now we have three employees — I just hired 2 back-end
engineers, one started this week and one started last week. We
are growing pretty aggressively!

As for users, any hour of the day you will see people buying and
selling stuff on Gumroad. Traffic is pretty significant. My
goal with the launch was to have maybe a few hundred, maybe a few
thousand dollars worth of sales, but it's a lot higher than that.
It's much higher.

How does Gumroad make money?

When our users make money, we make money. We take 5 percent
instead of a monthly subscription fee. A lot of sites take money
every month regardless of whether or not their users sell nothing
or $1 million dollars worth of stuff.

I think that's a really weird way to make money. I think the best
businesses are tied into the product. So for me it's like, ok if
you make more money, we'll make more money so the only thing we
can really do is to make our product even better. It aligns
everyone's interests.

It's the same reason we give investors equity. If we do well,
they do well.

A lot of businesses aren't like this. Facebook, for example,
isn't like this. Neither is Pinterest or Twitter. But if I have
the ability to build a product and a business that does have this
kind of trend, just like Airbnb, we should take advantage of it.
Facebook might spend a ton of time building the best product ever
for users but when it needs to make money it tacks on advertising
and screws over users in a sense to make advertisers happy.
That's not for me.

I raised $1.1 million with basically a weekend's worth of work. I
knew most of the investors previously. It took about four days to
raise the round.

It is a very momentum-driven game and I just had a lot of
momentum leaving Pinterest.

Is the plan to create an entire marketplace on Gumroad or
will it always be focused on personal selling pages?

Our focus is right now to nail the commerce piece. If you have a
Twitter account and you have a bunch of followers who want to buy
stuff we should be the best tool to use to sell to your
following. Once we have nailed that then we will probably start
doing other interesting things — but I have no idea to be honest.

I think Twitter and Facebook will get smarter and smarter.
Gumroad could just be a standalone tool that fits super well into
all of those other platforms.